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CHEBI:16483 - isonocardicin A

ChEBI IDCHEBI:16483
ChEBI Nameisonocardicin A
Stars
DefinitionA nocardicin in which the β-lactam moiety is substituted at position 1 by a carboxy(4-hydroxyphenyl)methyl group and at position 3 by a [(2Z)-2-(hydroxyimino)-2-(4-hydroxyphenyl)acetyl]nitrilo group in which the phenolic hydroxy group is substituted by a (3S)-3-amino-3-carboxypropyl group.
Secondary ChEBI IDsCHEBI:6033, CHEBI:14470, CHEBI:24904
Last Modified7 November 2018
DownloadsMolfile
FormulaC23H24N4O9
Net Charge0
Average Mass500.464
Monoisotopic Mass500.15433
SMILESN[C@@H](CCOc1ccc(/C(=N/O)C(=O)N[C@H]2CN([C@@H](C(=O)O)c3ccc(O)cc3)C2=O)cc1)C(=O)O
InChIInChI=1S/C23H24N4O9/c24-16(22(31)32)9-10-36-15-7-3-12(4-8-15)18(26-35)20(29)25-17-11-27(21(17)30)19(23(33)34)13-1-5-14(28)6-2-13/h1-8,16-17,19,28,35H,9-11,24H2,(H,25,29)(H,31,32)(H,33,34)/b26-18-/t16-,17-,19+/m0/s1
InChIKeyCTNZOGJNVIFEBA-MOKAZRKYSA-N
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
ChEBI Ontology
Outgoing Relation(s)
isonocardicin A (CHEBI:16483) has functional parent D-4-hydroxyphenylglycine (CHEBI:15695)
isonocardicin A (CHEBI:16483) has functional parent L-homoserine (CHEBI:15699)
isonocardicin A (CHEBI:16483) is a aromatic ether (CHEBI:35618)
isonocardicin A (CHEBI:16483) is a dicarboxylic acid (CHEBI:35692)
isonocardicin A (CHEBI:16483) is a nocardicin (CHEBI:25572)
isonocardicin A (CHEBI:16483) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
isonocardicin A (CHEBI:16483) is a phenols (CHEBI:33853)
isonocardicin A (CHEBI:16483) is tautomer of isonocardicin A zwitterion (CHEBI:142510)
Incoming Relation(s)
isonocardicin A zwitterion (CHEBI:142510) is tautomer of isonocardicin A (CHEBI:16483)
IUPAC Name 
O-{4-[(1Z)-2-({(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}amino)-N-hydroxy-2-oxoethanimidoyl]phenyl}-L-homoserine
Synonyms  Source
isonocardicin AKEGG COMPOUND
1-azetidineacetic acidKEGG COMPOUND
Manual XrefsDatabases
C00927KEGG COMPOUND
C00927KEGG COMPOUND
Registry NumbersSources
Reaxys:5324091Reaxys
Citations